Night time at the Griffith Observatory in the Hollywood Hills of Los Angeles. Take your tripod, awesome panoramic shot of Los Angeles.
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I really recommend you buy a copy of Syl Arena's Speedliter's Handbook before buying anything else!
I have a pair of 24" Ezyboxes, and a 12x48" stripbox. They're all very robust, the Ezyboxes are easier to set up (they just spring open and you attach the diffusion panel(s) with Velcro. That size (up to ~600 in2 surface area) is about as big as you'd want to go with a single Speedlite. Bigger modifiers need a monolight or a bracket to hold multiple flashes. For the 24" boxes, I have the fabric grids to limit spill, and one set of shaped diffusers (I really only use the round one, for catchlight shape).
For the light stands, as with everything, there are cheaper and more expensive ways to go. For outdoor use, you'll want something tall, and strong enough to take a sandbag on the base (softboxes can catch the wind like a sail, although umbrellas are worse). I have several Manfrotto light stands (two each of 1052BAC, 1051BAC, and 1004BAC). The 1051 is indoor only (small footprint), the 1052 is ~8', likely still short for outdoor use. All of them are robust, they fold flat (vs. round like a tripod) for easy transport/storage, and stands of the same size lock together when folded.
One stand you might consider is the Manfrotto 420B - it's a combination light stand (12') and boom. A boom is great because you can get a light out over the subject, and the Combi Boom lets you do that when you need to, and works as a normal light stand otherwise. The only reason I don't have one is that I have the Manfrotto 024 boom, which I mount on a 1004BAC and sometimes use to hold a monolight. The 420B will hold a Speedlite and 24" box fine.